


To the moon and back

by theolpha



Series: On the road to Bottom!Derek [3]
Category: Teen Wolf (TV)
Genre: Anal Sex, Blow Jobs, Bottom Derek, Face-Fucking, Fingerfucking, M/M, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2013-11-22
Updated: 2013-11-22
Packaged: 2018-01-02 09:22:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 6,512
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1055120
Author URL: https://archiveofourown.org/users/theolpha/pseuds/theolpha
Summary: <blockquote class="userstuff">
              <p>Stiles finally gets the chance to fuck Derek, and it goes perfectly.</p>
            </blockquote>





	To the moon and back

**Author's Note:**

> It took me almost four months to write/post this. This story is for [Natalie](http://shipsanddip.tumblr.com/). I asked her what were her kinks and [here's](http://shipsanddip.tumblr.com/post/57433214229/hello-there-what-kind-of-kinks-do-you-like-to-read-in) her answer. I don't know if it's what she wanted, but eh.
> 
> MASSIVE thanks to [Ryan](http://awildgrantaireappeared.tumblr.com/) who beta'd it. However, please note that English isn't my native language, and that I changed a lot of things AFTER sending the last version to Ryan. So any mistake are mine.
> 
> Try to enjoy !

Every time Stiles was back in Beacon Hills, an unofficial meeting pack took place at Derek's loft in order for Stiles to catch up with everything and everyone all at once and tonight was no exception. Until then, however, he needed to spend some time with his dad which usually consisted of watching TV lazily sprawled on their couch and commenting on every awful thing they heard.

“See you tonight” Stiles said leaving a quick kiss on Derek’s lips. Derek watched him leave and once the door was closed he went straight to his couch to grab the book he let there earlier. Three chapters later, he dropped the book again and grabbed his phone in order to let everyone know when they all should be here and that if they wanted to eat/drink they better bring their own junk food.

When Stiles arrived at his old house, he was welcomed by his dad and Scott, who was too eager to see his best friend to wait until tonight. After receiving two big bear hugs, Stiles went to the living room and waited to be joined by the two other men. They watched TV until Scott's phone rang in his pocket and quickly read the text. “Oh sorry, I've got to go. Some grocery to do for tonight. See you later Stiles! Sheriff.” And without another word, Scott was out.

The Sheriff gave his son a weird look and Stiles' only answer was the thing he knew best. He lied. “Bro-time,” he said with a shrug. “I think I'm going to hear about Allison all night.” He rolled his eyes at his father showing him how his plans for the night were lame. It was actually a lot more complicated than that: his father thought he would sleep at Scott's, Scott thought that he would sleep at home, while what Stiles was really going to do was having sex with Derek. But before that could happen, there was a big reunion with his other friends planned at Derek's and his father didn't know about that either.

_[…]_

When Stiles arrived at Derek's loft, he was welcomed by Lydia, Scott, Isaac and Derek of course. Seeing Scott without Allison was a bit weird, but Stiles assumed she must have stayed on her campus. Usually, they tried to be back all at the same time if possible but sometimes it just didn't work. Maybe she had an exam to study. Anyway.

All of the guests were sitting on the floor, even though there were two couches, large enough to have five people on them. Stiles went straight to where his friends were, closing the door behind him and sitting next to Derek, facing the three others. As soon as he sat down, the talks started again and soon enough, Isaac, Scott and Lydia started to criticize Derek's way to deal with werewolf business. Sensing Derek's eyes starting to roll with annoyance, Stiles silently and discretely took his hand behind their backs in silent support. When the contact between their hands was made, Derek felt the pressure being lifted off of his shoulders and instantly relaxed. Stiles even succeeded to change the subject very quickly and once the complaints were dropped, he let go of Derek’s hand. Most of the common topics were discussed and after about an hour of various talks, their mouths were desperately dry. Lydia took it as her cue to make a comment. “If Derek was a good host, he would offer us a drink.” Derek gave her a narrowed look she didn’t catch because she was doing something on her phone, and Derek still stood up.

He started towards the kitchen before turning back. Pointing to everyone he asked them what they wanted to drink. In his own particular way. “Coke? Coke? Coke? Great! Coke for everyone.” And he went back to the kitchen without another glance back.

Stiles had disbelief written on his face, as if Derek had just offended him. When Isaac silently raised an eyebrow at him, he simply answered: “He didn't even ask me what I want.” It was actually just an excuse to join Derek in the kitchen, so he stood up and went to meet his secret boyfriend. When he arrived in the kitchen, Derek was standing with his back turned toward Stiles and had his nose buried in his fridge. He'd barely taken the third can out, when Stiles was there, suddenly right behind him.

“What if I don't want coke?” Stiles asked as he grabbed Derek's hand knowing that here in the kitchen they were safe from other's eyes.

“I don't have anything else. It's either coke or water.” Derek turned to face Stiles and dropped a light kiss on Stiles cheek knowing that with two werewolves in his living room, any sounds could be heard. He circled Stiles with his strong arms before adding: “I told you all to bring your own drinks and as usual nobody listened!”

“Right. Coke then. Do you need help?” he asked quite loudly in order to make the other in the living room hear him and hide the sounds Derek was making as Stiles was running his fingers up and down his nape.

“No Stiles, I think I can handle five cans.” Derek used his annoyed voice but Stiles didn't buy it. He knew better. He smiled at him not letting his hand drop. He had just spent an hour next to Derek almost unable to touch him despite their obvious proximity. He stayed like that, completely ignoring what was currently happening back in the living room.

_[Meanwhile]_

“When are they going to stop the show? Can't they tell we all already know?” Isaac asked with a low voice. Sometimes, Isaac and Scott talked about Stiles and Derek. The fact that both of them were at the same university, near Beacon Hills, helped them to build a stronger friendship. They even shared an apartment, where Allison dropped by sometimes when she missed her boyfriend too much. When they were all three reunited, they were suckers for gossip.

“I bet they're proud and think they're subtle.” Lydia answered without looking away from her phone screen. She was probably texting Allison to let her know the mood around here or just a new boyfriend. The conversation was about to continue when an awkward silence felt upon them. Lydia put her phone back next to her the moment Stiles decided to appear back in the living room. He sat back down on the floor and watched everyone in the room with a suspicious look. “What?”

Scott blushed and looked at Lydia who sat still and unaffected. Isaac just looked at Stiles with a blank expression, as if he had no idea what Stiles was talking about.

“Don't pretend there's nothing. You were talking and as soon as you saw that I was back, you stopped.” He waited for someone to talk, to tell him he was wrong and paranoid, but nothing came. He looked at Scott and asks again. “Scott?” He knew his best friend was the weakest. And by weakest, he meant most honest.

“I can't talk about it. Not here anyway.” And Scott pointed to the kitchen with his forefinger to imply that he wouldn't have this conversation with Derek around.

“Well do you want to go outside? In the bathroom? Somewhere?”

“Stiles! It won't help.” Scott pointed at his ear now.

Stiles rolled his eyes. All of this was ridiculous. Most of the people sitting here were still afraid of Derek but at the same time, they would mostly help him if he was in danger. Stiles looked at the others and once again, he waited but they all remained uncomfortably quiet. Stiles let a long sigh escape his lips, and writhed in order to get his phone out of his pants. He typed something quickly and Scott grabbed his phone which was lying next to him.

From Stiles: _Better?_  
From Scott: _I guess? IDK._  
From Stiles: _Come on! What's going on? It CAN'T be that bad!_  
From Scott: _We think we know smt, but if we're wrong it would create a weird atmosphere._  
From Stiles: _And if you don't tell me what I want to know, is2g I won't be speaking until the end of this meeting, and Derek will knows smt's going on. Last chance to talk Scott!_

Stiles punctuated his text fixing Scott with his eyes. Isaac went to the kitchen and Lydia started to play with her phone waiting for her drink. As for Derek, he was still in the kitchen. What was he still doing in there anyway?

From Scott: _Well, funny how you suddenly mention Derek in your text._

Stiles took his gaze away from his phone and eyed back at Scott directly with his eyebrow scrunched together. “What do you mean?” he asked out loud, with his eyebrows lowered and his eyes squinted. There was a heavy silence between them. Scott seemed to fumble with his phone and suddenly gave it to Lydia in order to make her read the unspoken conversation, looking for any kind of help.

Stiles lurched up almost losing patience. “I'm going to the bathroom, I give you two minutes, and when I'm back, I better have a text on my phone explaining the whole problem. You hear me?” He didn't wait for an answer, left his phone on the floor, and stomped the room.

“What do we do?” Scott seemed panicked even if it wasn't that big of a deal.

“Aw Scott, don't be such a child. Let me take care of this.” Lydia started to type something on Scott's phone. _"we think you and Derek have sex. Quite frequently tbh."_ She hit "SEND" and heard Stiles' phone ringing on the floor in front of them. That was the moment Derek chose to come back with cans in his arms and sat on the floor where Stiles had been. He pushed the phone out of his way without sparing a glance at the object, and Isaac sat back in his usual spot.

Derek seemed to be about to ask something but Isaac’s voice was faster to be heard. “Where is Stiles?” Isaac asked when he noticed the room was quieter than before. “Don't worry, he'll be back soon.” Lydia answered studying Derek to read his reaction.

In the bathroom, Stiles was leaning on the faucet and stared at his watch. Seeing that two minutes had passed, he stepped out of the room and into the living room, where Derek was waiting for him with the others. Stiles sat, took his phone and read the text. He peered at the screen and then at Scott, who pointed at Lydia, who raised an eyebrow at Stiles.

“Prove me wrong!” She simply said, shrugging. Isaac and Derek had no idea what was going on but didn’t bother asking, knowing that they would soon find out.

When Derek heard Stiles' heartbeat going a bit faster, he frowned and resisted the urge to touch him. He bent and read the text over his shoulder and copied Stiles reaction, watching Scott then Lydia. She remained still and drank her coke carefully not to remove her lipstick.

Derek put a gentle hand on Stiles' shoulder and whispered something in his ear, quiet enough that even Scott or Isaac couldn't hear. Derek regained his previous position and Stiles just closed his eyes and breathed in for a long time. Obviously, this conversation was meant to happen, but Stiles would have appreciated a little warm up. He opened his eyes and crawled straight to Derek, sat between his legs and in his arms. You know what they say: a picture is worth a thousand words.

Derek took Stiles' hand and kissed his palm. Stiles was suddenly reminded of their little time this morning, but it’s wasn’t the perfect time to popped a boner right now. Did Derek say that he loved Stiles' hand? He's pretty sure he did. Stiles looked up to see the reaction of his friends and was distraught by what he saw: Scott wrinkled his nose which told Stiles that he was quite disturbed by what he was seeing. Isaac had a blank expression clearly not giving a damn about this relationship. And Lydia.

Lydia had a big smile on his face. “I knew it. I told you.” She turned toward Scott and Isaac causing Stiles to do the same. “Oh Scott! Don't pretend this is new. Actually, if I remember correctly, you were the first to point it out!”

Scott blinked once, twice, and his natural expression was back on his face. “I know Lydia but there is a difference between knowing, and actually knowing.” Derek was silent behind Stiles but he leant his head forward to see if his boyfriend was still with them or if he'd slid into that weird phase where he was physically here, but without really being there. Derek smiled and dropped a quick kiss on his cheek. Stiles heard a weird noise from Scott, and glanced at him once again.

Scott raised his palm over his chest, defensively. “I'm not against you being all gentle and stuff. You know I'm not like that Stiles, but it's weird.” His gaze switched to Derek, letting him know that the next part was aimed at him. “This is so not... You? I might need a little adjustment time.”

The end of the evening passed quite quickly after that. Stiles left his place between Derek's legs eventually, but they kept physical contact. Around 1am Isaac and Scott stood, they grabbed their helmets and left to go back to Scott's on his motorcycle. Lydia left just after them, dropping a kiss on Stiles cheek. “Come see me before you go back to campus, okay?” Stiles promised he would and finally, they were alone.

Once everyone was gone, Stiles grabbed Derek's hand and turned to face him. “So... What do you want to do now? Watch something? I don't know.” Stiles caressed his boyfriend's hand with his thumb and waited for his answer.

Derek caught the drift and smiled gently. With everyone else, Derek was always grumpy, sassy and annoyed. But with Stiles in private, it was different. Derek was gentle, and always careful with his gestures as if afraid to break Stiles. It was ridiculous, but now, Stiles realized why Scott was uncomfortable earlier. “Or, we can go to bed, and finish what we started this morning,” Derek said with a smug smile painted on his face.

Stiles didn't need another word to lead Derek toward the room silently. He couldn't wait to have sex with him; he was just so horny all the time when he was around Derek. He'd barely closed the bedroom door when he started to undress, starting with his upper body, and ending with the lower parts. Once he was down to his underwear, he jumped onto Derek's bed, sat back against the headboard and waited to be joined. He opened his legs and automatically, his hand touched his dick through the thin fabric of his boxers. Derek licked his lips, a hungry look in his eyes, and removed his own clothes quickly save for his boxers.

Stiles watched as Derek crawled on his bed and once he reached Stiles, he removed Stiles' hand from his groin, replacing it with his body, bending to kiss him. His hands were gripping the headboard and framing Stiles' face. When their lips touched, Stiles put his hand against the nape of Derek's head and breathed heavily into the kiss, almost moaning. Derek rocked his hips seeking friction and let one of his hands play with Stiles' nipple.

In this position, it was easy for Stiles to grip Derek's ass. He pushed at his shoulders to break the kiss and when they were parted enough he admired the way Derek's lips were swollen. “Get up.” And Derek did, soon followed by Stiles. Derek buried his face in Stiles shoulder and pushed Stiles' boxer just low enough that only his cock was out of it. He breathed Stiles' scent wanting to remember it forever while Stiles put his hands on Derek' ass and kept touching him. Derek pushed off Stiles body only far enough to have room to grab Stiles' dick and he jerked him slowly despite the awkward angle.

But it was not enough and Derek wanted more so after placing one last kiss on Stiles' lips, he let go of his dick and started to go down, kissing his jaw line, then his nipple. He stayed there nipping and biting at the flesh he found. Being rewarded by the sound of Stiles' heavy breath, Derek lingered a little longer, playing with the other nipple. Stiles threw his head back and closed his eyes overwhelmed by the pleasure. Satisfied with his effect, Derek resumed his journey, he licked at Stiles' torso and finally, he was on his knees, Stiles was staring down at him, chest heaving with every intake of air.

Derek was waiting for something, anything from Stiles to encourage him to keep going. He rested his forehead on Stiles thigh and closed his eyes before letting out a long sigh, blowing on Stiles balls at the same time. With the feeling of air around his dick Stiles put his hand in Derek's hair. He tried but failed to keep his hips from rocking toward Derek's mouth.

Derek lifted his gaze to meet Stiles' and without breaking the eye contact, he licked his lips before starting to lick at Stiles' cock-head. One slow lick around the crown and when Derek finally looked at Stiles' dick, he opened his mouth and put Stiles' member in it. One of Stiles hands rested on his nape, while the other gripped his hair, following Derek's move. Derek made a little and almost silent happy whimper at the feeling of Stiles’ dick on his tongue.

For now, Derek knew he was in charge but knowing Stiles’ heightened sense of mischief; he might have other ideas for later. Derek tried to give Stiles everything he loved by deep-throating him and moaning at the same time to share the vibrations. The feeling of Derek's stubble against the sensitive skin of his balls made Stiles' body shiver from toes to head. He touched Stiles balls and started to roll them just before he pulled his mouth from Stiles' cock. He licked at the balls in front of him and caressed at Stiles' perineum at the same time making Stiles to open his legs wider to give him a better access.

Stiles threw his head back when Derek took Stiles' dick in his mouth once again. Stiles could feel his balls tighten and circled his dick tightly to fake a cock-ring and hold off his orgasm for later. Derek looked up to catch Stiles' eyes once more, and it just drove Stiles crazy to see his boyfriend, the alpha, on his knees in front of him. He grabbed at Derek's head with his hands to keep him in place and started thrusting, once, twice, three times before he heard Derek's chocking on it. He let go of his grip and Derek resumed action on his own, even if once in a while, Stiles' couldn’t help himself, and thrusted forward into Derek's mouth.

It was so good that he barely managed to keep the sound for himself. These obscene sounds were the motivations Derek needed to grab Stile's balls once more, and pressed them together lightly not wanting to hurt him. Stiles bit his lips and closed his eyes. His knees nearly gave out on him, suddenly overwhelmed by the intensity.

When he opened his eyes again, he noticed that Derek hadn't touched himself yet so he decided to take care of it. He grabbed Derek's hair, pulled and Derek stood, following the movement. Once they were both standing, Stiles leaned forward and kissed Derek, unable to resist the urge to taste himself on Derek's tongue.

He pushed Derek's boxers down, grabbed his dick and Derek instinctively took a step back and sat down on the bed. Stiles knelt on the floor in front of him and took his boyfriend's cock in his mouth. Derek was already rock hard and didn't really need much friction to start moaning with pleasure. He let Stiles do whatever he wanted to his dick, and just enjoyed it.

Stiles licked along Derek's shaft in slow motion, teasing, making Derek just want more, always more. He was too focused on his dick and Stiles’ mouth. His perfect mouth. And then, it was as if Stiles could hear his thoughts because he was suddenly licking his abs and lying down on Derek.

Derek's legs were parted and bent at his knees. “How should we...” Stiles sat and straddled Derek's hips considering the question, and the multiple possible answers. First option, Derek could ride Stiles so he could be in charge of everything. He would be able to decide when he would want more, when he would want slower, faster, deeper, everything. But for a first time bottoming and according to Stiles, it might be too much to handle. Second option would be to have Derek on his back with Stiles between his legs, just like how they were a minute ago. This option was probably the best because, Stiles wouldn't be able to go too deep in Derek, and he wouldn't be able to hurt him. The third option would be more comfortable for Derek, but he knows, he knows deep inside that it would make Derek protest. He looked up and Derek sensed that something was going on. Derek’s hands which were caressing Stiles’ back abruptly stopped any motion. “What?” His voice had an annoying tone in it and Stiles knew it was just going to get worse.

So Stiles started talking, reaching behind him to grab Derek’s hand and bring them back in front of him. “Well. Don't think this is some kind of joke. I swear to god this isn't and I think this really is the best position for you.” He stayed on Derek's hips and ran his hands down the torso below him, to distract him, pinching one of Derek's nipples. “You might be uncomfortable with it but trust my experience; this is the one that hurts the least when you are bottoming for the first time.” Stiles refused to meet Derek's eyes.

Unfortunately for Stiles, Derek knew him too well. He just knew when something was wrong with him. “Stiles?” He sounded impatient and he was now frowning. What Derek wanted was for Stiles to say what he had to say.

Stiles swallowed loudly, trying to remove the lump forming in his throat. “I think you should be on your hands and knees.” Stiles took Derek's hands again and placed them on his hips when his boyfriend tensed under him.

Derek left his hands where they were, but closed his eyes and sighed. “This was a bad idea.” He didn't really know what was wrong with him and this position. If Stiles said it was the best, he should trust him. But this wasn't about trust. Derek often proved that he trusted Stiles. Being on his knees wasn't that bad, but something inside of him refused to let go.

Stiles realized that an internal dialogue was happening in Derek's mind, but he didn't want to lose his chance to get laid once more. Blowjobs were awesome as foreplay, but clearly not enough for him right now! “Look!” he put his hands on Derek’s and lifted them until they reach his nipples. Without any second of doubt, Derek’s nails started to lightly scratch at the skin on Stiles’ chest. “I really, really want to get laid Derek. I don't want to hurt you and you are clearly against the idea of being in a doggy style. I don't mind being in whatever position you want me, so let's do it. Take me how you want, where you want. I just want to have sex with you. Now!” And with this being said, Stiles rolled off Derek and laid beside him.

Derek could hear the disappointment in his boyfriend's voice and he immediately started to feel guilty. He took Stiles hand; kissed his fingertips and then his palm. He rolled and ended up being half on the bed, half on Stiles. He could hear a sigh passing his lips and this time, it was Derek who was straddling Stiles.

He bent down and took Stiles' left nipple between his teeth. He bit it just enough to make Stiles lose control and felt his hands in his hair, pressing his mouth against his chest. He smiled against Stiles' desperation and was suddenly hit by how strong their relationship was.

He sat up and Stiles raised an eyebrow at him, silently asking _"what now?"_ Derek kissed Stiles on his lips, a chaste and quick kiss, and exhaled. “Let's do this.” And he rolled off Stiles. This time, instead of lying on his back, Derek was on his hands and knees.

Stiles stood up quickly and went behind Derek putting his hands on the hips in front of him. “Oh my god” he said while kissing Derek's tattoo and watching the heavy muscles in his back. He sat on his knees again and waited. The view in front of him was so beautiful.

Derek was facing the wall in front of him and felt extremely exposed being like this, bent and waiting for Stiles to do something. His hands went on the headboard and he rested his forehead on it when he felt Stiles parting his cheek and blowing a cool air down the crack of his ass. The sensation was mostly new even if Stiles had rimmed him in the past. But knowing that in a few minutes, his ass would be breached by Stiles cock, made it a brand new experience. He decided to concentrate on something else, and the first thing that came up his mind was to listen to Stiles’ heartbeat. It was faster than normal, but steady. It helped him relax.

Stiles let go of one cheek and instead, with his newly freed hand, he put a finger on Derek's hole. He caressed the flesh he found; knowing that pushing inside right now without lube of further preparation was going to hurt Derek. Stiles wanted for Derek to have the best first time bottoming ever. His desire to lick him was so intense that he just couldn’t resist the temptation. One lick and he could already hear Derek sighing his name, face still down on his forearms. He started down his balls, let his tongue travel Derek's perineum and finished on his ass.

His fingers gripped his ass cheek even harder, and he kept licking, again and again. “Relax Derek. I'm not going to hurt you.” Derek was so tight; he was going to need a lot of manual preparation before he was ready to take Stiles' cock. Derek writhed and pushed back against Stiles’ face, seeking for the sweet licks. Stiles used both hands to open Derek's cheeks even further, and pushed his tongue into Derek's hole, as deep as it would go.

Derek let a cry of pleasure escape his lips involuntary but wasn't ashamed of it. He loved this feeling and knew that he was already getting addicted to it. He loved to be rimmed but at the same time, he just wanted it to end, so he could feel what it was like to have Stiles inside of him. “Stiles, please.” He turned his head to try and catch a glimpse of Stiles but he only saw the top of his head moving. "Please. Put your dick in me." The pleasure was beginning to be so intense that he could feel his claws trying to pop out without his command. Fortunately, even if this had to happened, most of his fingers were hidden behind the headboard, and unable to scare Stiles.

Stiles withdrew his tongue from his ass and arched an eyebrow at him. Then he leaned toward Derek's bedside table to grab the lube. “Just a few fingers to open you a little more and you can have whatever you want Derek. Especially if you ask so nicely. I Promise.” Derek took the opportunity that they were almost facing each other to kiss him, just before Stiles went back behind him. He slicked two of his fingers and placed them in front of Derek's ass, but didn’t push just yet.

The anticipation was too much to handle for Derek. He buried his head on his forearms again and pushed back his ass, seeking a little more pressure from Stiles. He was soon rewarded and finally, finally he felt the first knuckles penetrated him. He clenched involuntarily and Stiles stopped all at once. “Hurt?” Maybe two fingers to start were a little too much.

Derek took a few long breathes, and tried to relax around Stiles' finger. “No- not exactly. It's just... Weird? But don’t you dare stop.” He turned his head and the look on Stiles' face was just breath-taking. He was flushed, and his eyes were watching where his finger was disappearing inside of Derek with a strong fascination. He met Derek’s gaze before nodding and then, Derek turned his face back to the wall as Stiles resumed his actions. He could tell that his pupils were on the verge of becoming red, and he was afraid to scare Stiles if he had to witness his loss of control during sex.

Stiles kept thrusting his finger, and smiled gently when he heard Derek's exhale at the same time. When his forefinger was deep inside Derek and without removing it, he started to push his middle finger along the first one. It might be too much but right now, it wasn’t what Stiles was thinking about. He couldn't wait to be inside of his boyfriend and just wanted this part to be over.

It was selfish, and Stiles suddenly realized it. He bent and bit Derek’s ass cheek. It seemed to push a button inside Derek because the little resistance remaining in his rim left him the second Stiles' teeth were on him. The fingers started moving inside of him and it was so good. Stiles was lost surrounded by all of these sensations. All of his senses were used with Derek: his eyes were watching his fingers, his fingers were touching Derek, in and out, the smell of sex was heavy in the air, and he ran his tongue again Derek ass cheek to fulfill his sense of taste. But what was the most amazing was to hear the loud sounds Derek did, unaware.

Stiles crooked his fingers, pulled them out a little, and pushed them back slowly. He did it once, twice before he let his rhythm go faster, bit by bit. Derek was fully relaxed now and even if the discomfort was still here, he preferred to focus on the pleasure Stiles' fingers brought in him. He put his head against his forearms, and used the leverage of the headboard to push back and take Stiles' fingers deeper.

“Derek” Stiles ran his free hand against Derek flank, and once he thought Derek was open enough, he removed his fingers completely and grabbed the lube to cover his neglected dick. He put a little bit of liquid on Derek's ass, thinking that too much of it couldn't hurt.

He stroked his cock quickly and put one of his hands on Derek's hips while presenting his cock in front of Derek's hole. “Stop me if I hurt you.” Derek nodded without saying anything else. Stiles began slowly but all of his preparation was almost vain when he saw Derek clenching around the very beginning of the head of his cock.

He ran his hand on Derek's back then around toward his torso, and started to play with the nipple he found here. He ran his nails on the flesh as a distraction, but it did nothing to help Derek, so he let his hand wanders down toward his dick.

He grabbed Derek's dick and circled it with his hand. He pressed it to focus Derek's attention in it and finally, he felt him relaxing. He pressed harder and pushed his cock deeper, slower and inch by inch. Derek straightened up bracing himself on the headboard and it only made his ass take Stiles' cock deeper. He winced and clenched around Stiles again, saying incomprehensible thing. Stiles removed one of his hands from Derek's body and leant down to tangle his fingers with Derek's around the headboard.

He was bottoming out but didn't move to give him time to adjust. “Derek?” His voice was concerned but Derek didn't answer. He dropped a kiss against his shoulder blade, worry starting to swell in him. Derek didn’t trust his voice right now, so once again instead of an answer, he just pushed his hips back telling Stiles that he could move; that he needed him to move.

Stiles was surprised by the movement but relieved Derek did it. It meant that he wasn’t just doing this to please Stiles but that he was also enjoying it. Derek seemed totally into it and Stiles couldn't do anything but thrust again and again. The pleasure was shared and hearing that Derek was trying to keep his moans silent, by biting his own arm, just turned Stiles even more, if possible.

Stiles could feel the vibrations in Derek’s chest resonated in his own body. It was overwhelming and he put his hand on Derek’s shoulder blade thrusting gently, not wanting to hurt Derek. Finally he received the sign he was waiting for: Derek pushed back on his cock matching every thrust. Stiles took his cue and sped up. Derek’s response was immediate and his breath became louder.

Once Stiles thought that Derek had enough of this position, he took his cock out of his ass and caressed one of Derek's ass cheeks when he heard a sound of protest. “Turn around.” It was a simple request that Derek was visibly eager to follow, not knowing what would come next. At this point, Derek really didn't care; the only thing he wanted was the feeling of fullness that Stiles inside of him brought. “On your back and bend your legs.” Stiles' voice was husky, and Derek wanted to hear this voice forever.

Stiles pushed Derek's legs up, and aligned his cock once again. Before pushing his dick in, he put his forefinger at Derek's hole and pushed one knuckle to gauge Derek's reaction. He barely had time to move his finger before Derek was back to moaning in pleasure. Stiles moved his finger just to see Derek's reaction and when Derek looked at him, he bent down to kiss him. “You have no idea how much I love you Derek.” He removed his finger and nipped at Derek's earlobe. Derek's large hands rested on Stiles' shoulders and he lost himself in the sensation of Stiles tongue on his ear. Stiles licked and nipped and suddenly, a sigh escape Derek's lips as Stiles pushed his cock back in his ass.

This new angle allowed Stiles to hit Derek’s prostate at every thrust and taking Derek’s cock in his hand. The picture that Derek made was intimate and Stiles wanted to see it again and again. With one hand on Derek’s cock and the other around one of his thighs for leverage Stiles spoke again. “You should see yourself right now.” Derek let breathy sound escape his nose to tell Stiles that he had heard him but said nothing. He was seriously too eager to think properly.

He could feel his orgasm coming and his toes starting to curl. His breathing became heavier and he opened his eyes to see Stiles’ expression. “I’m gonna come Stiles. Come on, make me come!” His voice was wrecked but he really couldn’t care less. Stiles caressed his thigh and turned his head lightly to bite it, stroking Derek’s shaft all at once. After the bite, he licked it and that was all it took for Derek to come with Stiles’ name dying on his lips.

His eyes switched red and Derek closed them and turned his head really quickly, but it was too late, and Stiles had already seen it. He stopped his movement at once and place one of his hand against Derek’s cheek. “Let me see Derek. Please.”

Derek reluctantly opened his eyes again, and his eyes were still red. Stiles bent down and drop a light kiss against Derek’s lips. It was chaste and intimate. Stiles stood and thrusted faster, losing his rhythm and he brought his come-covered hand to his mouth before licking his forefinger. Derek watched him with hungry eyes and completely spent, but wanting to make Stiles come more than anything. “Yes Stiles. Keep doing that.” He was cut off by a moan of pleasure he didn’t expect. He tried to clench around Stiles and after his second try, he felt Stiles going completely still before sensing a brand new sensation inside of him. Stiles turned his head slightly to rest his forehead against Derek’s knee, breathing loudly.

He pulled out of Derek very slowly once he was done, and sat on his knees to watch his mess coming out of Derek’s hole. It was fascinating and now, Stiles understood why Derek was so found of watching this happening to him. Derek closed his eyes and turned his head against his pillow, letting Stiles enjoy the show. After a while, he felt the bed shift with Stiles’ departure and he opened his eyes suddenly worried. Stiles stepped in the bathroom and came back with a washcloth to clean Derek. He smiled at him. “You can thank me later”. Stiles was so familiar with the sensation of being stuck in his own dried come. He swiped slowly at Derek’s hole and then on his stomach where a little of his cum had landed before. He went to the bathroom again, but this time he came back with a glass full of water which he offered to Derek. Stiles then reclined on the bed next to his amazing boyfriend.

Once the glass was empty, Derek put it on his nightstand and turned to face Stiles. He smiled and put an arm around his chest to bring him closer. He buried his face in the crook of Stiles’ neck and stayed there, tangling their legs together. Stiles shifted his head a little and placed a kiss on Derek’s forehead before combing Derek’s hair with his fingers. Derek shifted one last time to get the comforter on them and put his hand over Stiles’ heart as usual, ready to fall asleep.

“Thanks” said Stiles. If you asked Derek, Stiles was just thanking him for the new layer between them and the cool air of the room. If you asked Stiles, he was thanking him for letting him experience this.

**Author's Note:**

> By the way, you can find me on Tumblr [here](http://tueloup.tumblr.com/) or [here](aconitt)


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